反应详情

To a solution of isopropyl 1-[(1R,3S,4R,5S)-2,3,4-tribenzyloxy-5-[4-chloro-3-[(4-ethoxyphenyl) methyl]phenyl]-6,8-dioxabicyclo[3.2.1]octan-1-yl]ethyl carbonate 13a (244 mg, 0.3 mmol) in a methanol/tetrahydrofuran mixture (v/v=4/1, 10 mL) were added o-dichlorobenzene (0.16 mL, 1.5 mmol) and 10% Pd/C (36 mg, 0.03 mmol) in turn at room temperature. The mixture was stirred at room temperature under H2 for 4 hours and filtered. The filtrate was concentrated in vacuo. The residue was purified by silica gel chromatography eluted with PE/EtOAc(v/v)=4/1 to give the title compound 13 as a white solid (120 mg, 75.0%, HPLC: 92.3%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 537.3[M+H]+; and 1H NMR (600 MHz, DMSO-d6) δ(ppm): 7.40 (m, 2H), 7.29 (m, 1H), 7.11 (d, 2H), 6.84 (m, 2H), 5.58 (brs, 1H), 5.04 (brs, 2H), 4.93 (m, 1H), 4.73 (m, 1H), 4.50-3.98 (m, 5H), 3.54 (m, 2H), 3.44 (m, 2H), 1.31 (m, 6H), 1.23-1.20 (m, 6H).

1. filtrationfiltered
2. concentrationThe filtrate was concentrated in vacuo
3. customThe residue was purified by silica gel chromatography
4. washeluted with PE/EtOAc(v/v)=4/1